5 Things No One Tells You About Leaving Teaching

5 Things No One Tells You About Leaving Teaching

Leaving teaching is no small decision—it’s a leap into the unknown that’s equally terrifying and liberating. While there’s no shortage of advice on why or when to leave, the road ahead comes with surprises. From navigating unemployment benefits to adjusting to a world that doesn’t revolve around bells and lesson plans, here are five things no one tells you about life after the classroom.

Milton from Office Space, sitting at a desk with a red stapler. The text reads 'If they take my stapler, I'll set the building on fire'

Let’s start with a gentle warning about the muggles: they have different social boundaries. You’re now navigating a world of mental toddlers who think every hiccup is a crisis or, worse, want to debate politics over coffee like it’s a team-building exercise. Treat coworkers with acceptance and a healthy dose of fear, as you would a kindergartener with a glitter shaker, and you may escape with minor casualties.

While you grapple with their quirks, don’t forget—they’re scratching their heads over yours. You’ll realize your favorite teacher stories are the conversational equivalent of grading essays on a Saturday. Sure, everyone will ask why you left, and that’s the perfect opportunity to share a well-crafted, humorous anecdote (it wasn’t the first but the second time a kid peed on the rug that I decided…). After that, keep it light. No one outside the teaching bubble is interested in the chaos of the classroom.

The reverse is also true. The absence of 150 kids vying for your attention will make you feel much better, but curb your enthusiasm to shout it from the rooftops. Nobody wants to hear how easy their job is—it’s the corporate equivalent of telling a toddler their crayon drawing sucks.

A golden ticket with the text 'Career Change Golden Ticket'

Here’s a harsh truth: You don’t get unemployment insurance if you quit, and that’s a shame because you paid into it your entire career—you deserve a bite of that pie. I was laid off and eligible for $700 a week and that cushion made all the difference.

If you have a good relationship with your principal, you could try the long shot and ask to be let go. Alternatively, you can take your foot off the gas, allow things to slide, and hope to get non-renewed. It’s not always possible, but if there’s even a slight chance, it’s worth considering. After all, you’ve already earned it—you might as well use it.

Let’s be real: We shouldn’t let high schoolers pick a career without at least apprenticing. I was barely old enough to drive when I chose to teach, and nobody tried to convince me otherwise. The first time someone did, I was already in my teaching placement. A seasoned veteran looked me straight in the eye and said, “Get out before it’s too late.” I should’ve listened.

My teenage dream was to be a truck driver—travel, see states, just drive. Instead, I went to college because it wasn’t optional, but I should have reflected on what I wanted before locking into a career.

Looking back, I wish someone had told me to brainstorm careers that fit my lifestyle and interests. It’s never too late, by the way. What excites you? What makes a perfect workday for you? It might take some upskilling to get there, but if there’s one thing teachers are great at, it’s learning.

For example, after I left teaching, I spent a year in an electrical apprenticeship. It wasn’t for me in the end, but it was a phenomenal learning experience and gave me a better understanding of what I want—and don’t want—in a career. That’s the beauty of stepping outside the classroom: there’s so much more out there. You just have to try.

Image of a hand reaching out to catch a falling piggy bank

If you’re close to your pension vesting, do yourself a favor: wait it out. My pension vested after seven years, and that’s when I got out (luckily). If it’s not vested, you could lose most—or all—of it.

But here’s the catch: teachers often fall into this binary trap. Either you’ve “invested too much to throw it away,” or you’re convincing yourself to “just stick it out a little longer.” Before you know it, “a little longer” turns into retirement, and you’ve spent your entire career waiting for the light at the end of the tunnel—only to realize it’s just the copier on fire again.

If you can tough it out until your pension vests, great. If not, I get it. But if you’re weighing your options, it’s worth considering how much that extra time could mean for your future. Either way, don’t let the system guilt you into staying longer than you need to—it’s your life, not theirs.

two illustrations: on the left a teacher juggling tasks, and on the right a woman sipping coffee and working on a laptop

When teachers enter the office world, it’s immediately clear: you’re absurdly productive compared to most coworkers. Years of surviving in a system where proper planning isn’t optional—yet planning time is practically nonexistent—have conditioned you to do more with less. But in my second career, I found the opposite to be true. Deadlines existed, sure, but the stakes for missing them felt so low that staying on time became optional.

This superpower of yours can be a double-edged sword. On the one hand, it can boost your confidence and set you apart. You’ll probably finish tasks faster than anyone else, and people will notice. On the other hand, it’s okay to let go of the teacher’s mindset and slow down. You don’t have to pick up your coworkers’ slack, and honestly? I wouldn’t recommend it.

I’ve embraced the slack. If the deadline allows for extra time, why not take it? As long as your work is solid and your reputation stays intact, there’s no need to push yourself to superhero levels of productivity. You don’t have to “just keep swimming” anymore—you can join the current and let the flow carry you.

illustration of a ship sailing into the horizon

Leaving teaching is like stepping into uncharted waters—it comes in waves, and no two journeys look the same. Whether you choose to go with the flow or ride the waves, the key is finding what feels right for you. Every experience, even the rough ones, teaches you something valuable. So, enjoy the calm when it comes, steady yourself for the storms, and embrace the thrill of the unknown. After all, no grand adventure ever started in the safety of a harbor.